The following is the email interview we conducted with Lori Gottlieb's ex "Tim," condensed slightly and with our questions in bold.

Can you describe how you got in contact and how the relationship started?

Other than the "Ralph and Alice" conceit [Gottlieb says the two referred to each other by the names of Honeymooners characters], which she never expressed to me, she gets a lot of that right. I sent her fan mail based on her stuff in Slate and Salon, which was intelligent and funny stuff, though it looks a lot different now with perspective. (For example, she pretty much stated the thesis of Marry Him in something she did for Slate in 1998 where she compares searching for a mate with searching for a parking spot: do you jump in the first space you find, or do you circle the lot endlessly trying to find a spot near your destination? And might you lose a good-enough space by looking so hard for the best space?) I had no romantic expectations; I was just a frustrated writer in a lawyer's career who sent emails to lots of writers whose stuff I liked.

But she pushed to speak on the phone, and to meet. We had a dinner at an Italian restaurant (where I most certainly did not speak about my penis or give her a rose), and I didn't think anything of it. I was quite confident that she viewed me as out of her league (especially when the valet pulled up with my Chevy Malibu and she expressed surprise because she didn't know anyone who drove an American car); too, my wife had just left me three months earlier and I wasn't going to be asking anyone out just yet. So we muddle along platonically for a couple of months; she even gives me a speech where she explains all the reasons she couldn't possibly go out with me romantically, and I shrug my shoulders. Yeah, it would be cool to date someone with her resume and sense of humor, and she's Jewish to boot, but not too Jewish, and she's physically attractive, but I had no expectations that it was going anywhere.

But eventually I get the sense that she's protesting too much; she wants to see me several times a week, she's calling me a lot while I'm at work, she's emailing me all the time. This gets confirmed in February when I go off on a weekend trip with a woman I knew from my hometown, and Lori completely freaks out because she calls my apartment on a Saturday night and my roommate won't tell her where I am. (This is 1999, and I don't own a cell-phone yet.) [...]

[The next week,] We get to talking on her couch, and I kiss her. She starts to go through her list of reasons why she can't date me, and, very unusual for me, I kiss her a second time. But I'd guessed right, she kisses back, and she's surprised that I know how to kiss and can handle foreplay, and we end up in bed. (In bed. We never slept on the floor.)

Was Gottlieb openly judgmental about your weight?

And then some. It was part of the criticism sessions we'd have about once a week where she would tell me everything that was wrong with me. It wasn't enough that I was going to a gym, I had to go see a particular personal trainer, a particular therapist. My nutritionist put me on a 1600-calorie/day plan, and Lori was second-guessing that. I'd put a tiny squirt of mustard on something, and Lori would ask whether that was part of the diet, and I'm like, "Chill, it's not even five calories." And this is all while she's finishing up her memoir about her path back from childhood anorexia.

Oh—and she'd weigh me every morning that I slept over, and ask about it on other days. Yeah, I don't know why I put up with that either.

What was good about the relationship?

Well, the good news was I went from 265 to 235 pounds in a short period of time. It was like having a 24-hour personal trainer who also slept with you for the cost of a handful of sushi dinners a week where we always ordered the exact same thing.

And, to be fair, I was socially inept, almost autistically inept, and her bluntness about it did make me a lot less nerdy as I learned rules about social interaction and how to answer questions like "Where are you from?" and "What are you working on these days?" without going into RainMan-length monologues.

I was really down about my divorce, which had stranded me in a strange city where I didn't know anyone and left me with a lot of debt from alimony and paying my lawyers and my wife's. So I got a self-esteem boost at a time when I needed one. And she got someone whose intellect she respected but regularly validated her with praise and flowers and let her get her uncompromising way all of the time.

It took a while, but I eventually came to realize how unhealthy all this was [...]

Did you get a general sense of Gottlieb's attitude to dating? Was she looking for marriage, family?

I got the sense that she was looking for marriage and kids, but she kept starting conversations with me explaining all the reasons why I couldn't be the father of her children or why we could never be together forever. So it was never really clear to me what her motivations were. My best guess is that I reminded her of her smart and successful father, and she was trying to resolve some issue there. My second-best guess is that she lives her entire life as if on a stage, and she viewed dating me as a ready source of dramatic comedy or comedic drama.
She talks a lot in her book about mistakes she made in her dating life. Do you feel that when you were together she had a "dating checklist?" Or that she wanted men she was with to look or act a certain way?

Absolutely. The one time we went out for ice cream, she told me it was a good thing I didn't order vanilla, or she'd lose a lot of respect for me. [...] Presumably, in conjunction with the American car, it would've been a dealbreaker.

My ex-wife liked facial hair, so I had a beard that I shaved the week before I met Lori, and she mentioned that everything would've been different if I hadn't shaved.

Everything was a test. One afternoon, she calls me at work and tells me I have to come over immediately to kill a spider. I'm like "You realize Diane Keaton already did this in Annie Hall, right?" No, it was evidence of whether I really cared about her, would I stay at work and finish the assignment the senior partner wanted on his desk in two hours, or would I drive to Brentwood and kill the spider for her. So, yeah, that spider made me have to switch law firms and lose several years before I could become partner. Most expensive spider in the world. My fault for giving into the emotional blackmail, but, hey, I'm a naive romantic.

From your point of view, how and why did the relationship end?

It was doomed when I started asserting myself, which meant that our arguments came more often and involved more screaming. Because it was never enough to capitulate and let Lori have her own way, we then had to have a meta-argument where I confessed the errors in reason and logic that prevented me from seeing things her way in the first place. And for some reason, I had the nature that could compromise on the argument, but had no patience for the meta-argument, and I would start a meta-meta-argument, which would just make tensions worse. I stormed out of her place a lot. (She never came to my place, because she didn't go "east of LaCienega." I guess that's what the kids are calling it these days.) She would say she loved me, and sign all her emails with that sentiment, but would at least weekly put me through these emotionally battering monologues about how my weight and other failings were preventing us from being really serious.

I had no outlet for my resentment, so I started "cheating" on her—first with food, then with an entirely inappropriate fling with an 18-year-old who was rotating her social life around three or four LA lawyers at the same time and gave me 10% of her time. Only time I ever cheated on a girlfriend before or since, and I realized it wasn't in my nature.

So I tried to break up with Lori, and out came the drama [...] Yes, she'd been horrible to me, she admitted, but she'd make it up to me later once everything calmed down. She needed me, she loved me, how could I leave her? She got her way again.

Nothing really improved in the relationship; I'm still getting regular lectures; and she chooses to go to Stanford instead of UCLA, where she could've gotten in-state tuition and stayed in the same city, but is paying a lot extra to be able to say she went to Stanford. So I see the writing on the wall: no way a first-year med student is going to have time for a long-distance relationship with someone she's regularly lecturing on his inadequacies. No, no, she says, don't break up with me, I love you, long distance is fine.

Against my better judgment, I believe her. I take time off of work to drive her from LA to the Bay Area to help her find an affordable place to live near campus (but she wants a white neighborhood) and then a second drive up to handle her move. She skips an opportunity to come to LA before classes to give me moral support at the hearing where my divorce is finalized. And, then, of course, breaks up with me the day before classes start.

And drops out of med school a year later, though not before writing a piece for Time [link added] about how her non-traditional background was going to make her a better doctor than her classmates.
Have you read "Fat Like Him" in its entirety? If so, what was your reaction?

Yes.

I learned of it by accident: my favorite ex-girlfriend (a Jezebel commenter, natch) was writing book reviews for a website, so I read her reviews, and noticed another book review in the same article criticizing an "appalling" "self-congratulatory tale of having actually dated a fat guy." And I immediately associated "self-congratulatory" with Lori Gottlieb. I checked with the reviewer, and she confirmed that it was Gottlieb who wrote the story, but she changed [nickname redacted] into "Tim." The reviewer suggested that I probably don't want to read it.

So, she broke her promise that she wasn't going to write about me. Not a big surprise, I guess, even if it's something out of a Jennifer Weiner novel.

I email Lori and ask her for a copy. She tries to create a guilt trip: how dare I bother her with this when she's suffering medical problems [...] that keep her from spending more than an hour a day on-line. When I phone her, she says I need to read it first.

So I read it, and try to make a joke out of it, sending this email the day I read the short story:

Hope [you're] feeling better.

I figured you weren't going down on me because of your general
squeamishness about bodily fluids or some calorie concern or the
other. But I read that you were giving Tim regular blow jobs, and the bozo
weighed at least 50 to 80 pounds more than me and didn't even fit in
your bed. Imagine how grumpy I am.

No response.

But I was offended; this is a non-fiction book, and she's making up stuff to fit an arc or for a joke or to make her look better. So Tim is 300 pounds, and gains 50 in the month before the break-up, while I went from 270 to 235 to 245; Tim was a member of Overeaters Anonymous and I wasn't; Tim has a variety of disgusting physical features beyond his obesity; Tim obsesses about whether he can see his penis; Tim plaintively asks Lori to reciprocate his love, when in real life Lori used the L-word first; and the multiple times Lori begged me to stay with her and her broken promises are left out, of course. There were ten months we were emailing, and seven we were dating; Tim's only in the picture for five months.

I complain about this to her, and she's completely unapologetic: it's "creative non-fiction" so it's okay to make up stuff. If only James Frey thought to tell Oprah that!

The bit about the partner at my law firm hitting on Lori in front of me happened; so did the bit about Lori's friends surprising us in the middle of sex so they could get around her attempts to hide me from them (though, to her credit, in real life, Lori acknowledged who I was; there certainly wasn't pizza involved). I can objectively recognize those as funny stories. I've read Philip Roth novels. I would have nothing against a autobiographical short story that's labeled as such, even if the main character is a fictional person with the same name as Lori.

But even with all the fictional ducks lined up in a row to make herself look better, she comes off as vile and self-unaware in that story. So she's hurt herself more than she hurt me.

So, yeah, I'm annoyed that she broke multiple promises to me, then makes up stuff about me to self-aggrandize herself, then is unapologetic about it or failing to give me a heads-up. And I'm also annoyed that even now she's ashamed of me. When close friends of mine end up on writing projects with Lori, and I ask them to say hello to her for me, she pretends she's never heard of me. I've heard of name-dropping, but that's name-lifting. Not sure what she accomplishes by that, all my friends come back to me and quizzically ask "What's up with her?" And I guess I'm angry enough to enjoy the Jezebel threads and volunteer my personal experience.

But this is what she does with her writing to everyone in her life: her parents; her classmates from two different schools; her co-workers at two different jobs; her lovers; her son, Baby Book Deal Gottlieb. She's eventually going to run out of bridges to burn.

What's your reaction to Marry Him and Gottlieb's general message that women should settle for "Mr. Good Enough"?

There was certainly some schadenfreude with the original article. My fiancee would snuggle up to me and said "I'm glad she didn't settle for you."

Of course, four months later, I went on a business trip, and my fiancee suddenly decided that I was too physically unattractive for her, and moved out and ended a three-year relationship without any warning or even a face-to-face conversation, so perhaps the last laugh is on me.

The thing is, Lori knew all about the satisficing strategy and was writing about it when she was 30, so the idea that it's this new epiphany in her 40s is just bullshit.

Every book or article Lori writes has nothing to do with the subject of the book: they're all about making Lori look more attractive. She's the precocious-but-troubled eleven-year-old grown up into a real size 0 who partakes of milkshakes; she's the Internet executive who saw through the bubble before it burst; she's the wise and witty dispenser of relationship advice. She still has the anoxeric's desire for control, and it's about controlling her image.

And this book is no different: it puts forward the persona of Lori Gottlieb as a famous anti-feminist writer of best-selling books and controversial Atlantic essays, which is a much more attractive persona than the 40-something single mother who could never commit to any of her boyfriends. And she'll tell her husband-to-be that she thought she had to settle, but is glad she didn't have to after all. And then that book will be Lori's version of Elizabeth Gilbert's "Committed." Then there will be a book about her soccer-momhood, and how she does it better than the other moms or her own mother. Maybe even a book like Sandra Tsing Loh's about leaving her husband for a more exciting guy after that. Not necessarily because there's something wrong with her husband, but because it would make a much better movie deal if there was conflict and an arc.

Anything else in FLH you'd like to clarify or set straight?

I didn't go to an Ivy League school or graduate first in my class. I found it funny she had to inflate my resume to make her look better in the short story.